Abstract
Abscisic acid (ABA) regulates many important processes in normal growth and development as well as in adaptive responses to environmental stresses. For correct and accurate actions, physiologically active ABA level is controlled through fine-tuning of de novo biosynthesis and catabolism. Hydroxylation at the 8′-position of ABA is the key step in the oxidative catabolism of ABA, and this reaction is catalyzed by ABA 8′-hydroxylase, a cytochrome P450 (P450). Recently, the CYP707A family of Arabidopsis has been identified as ABA 8′-hydroxylase through genomic and biochemical approaches. The CYP707A family is present in a wide range of plant kingdom and functions in ABA catabolism in plants. CYP707A is the pivotal enzyme controlling the endogenous ABA levels by its transcriptional regulation and plays a key role in ABA-mediated physiological processes such as seed dormancy and stress response. Specific inhibitors of ABA catabolism can manipulate ABA homeostasis in plants and are potentially very useful tools for cellular and molecular investigations in the field of plant physiology as well as for potential agricultural chemicals. Identification of the ABA catabolic genes gives us new insight into the development of chemical inhibitors specific to ABA 8′-hydroxylase.
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References
Abrams SR, Rose PA, Cutler AJ, Balsevich JJ, Lei B, Walker-Simmons MK (1997) 8′-Methylene. Abscisic Acid 114:89–97
Addicott FT (1983) Abscisic acid. Praeger, New York
Asami T, Yoshida S (1999) Brassinosteroid biosynthesis inhibitors. Trend Plant Sci 4:348–353
Arai S, Todoroki Y, Ibaraki S, Naoe Y, Hirai N, Ohigashi H (1999) Synthesis and biological activity of 3′-chloro, -bromo, and -iodoabscisic acids, and biological activity of 3′-fluoro-8′-hydroxyabscisic acid. Phytochemistry 52:1185–1193
Audenaert K, De Meyer GB, Hofte MM (2002) Abscisic acid determines basal susceptibility of tomato to Botrytis cinerea and suppresses salicylic acid-dependent signaling mechanisms. Plant Physiol 128:491– 501
Bajguz A, Asami T (2005) Suppression of Wolffia arrhiza growth by brassinazole, an inhibitor of brassinosteroid biosynthesis and its restoration by endogenous 24-epibrassinolide. Phytochemistry 66:1787–1796
Choe SW, Dilkes BP, Fujioka S, Takatsuto S, Sakurai A, Feldmann KA (1998) The DWF4 gene of Arabidopsis encodes a cytochrome P450 that mediates multiple 22 alpha-hydroxylation steps in brassinosteroid biosynthesis. Plant Cell 10:231–243
Chono M, Honda I, Nakamura S, Abe F, Kaneko S, Watanabe Y (2005) Analysis of the regulation of abscisic acid content in barley lines with the different levels of grain dormancy. Regulation of Plant Growth & Development, vol 40 Supplement 2005. The Japanese Society for Chemical Regulation of Plants, Tokyo
Correia MA, Ortiz de Montellano PR (2005) Inhibition of cytochrome P450 enzymes. In: Ortiz de Montellano PR (ed) Cytochrome P450: structure, mechanism, and biochemistry, 3rd edn. Kluwer Academic/Plenum Publishers, New York, pp 247–322
Cutler AJ, Rose PA, Squires TM, Loewen MK, Shaw AC, Wilson Quail J, Krochko JE, Abrams SR (2000) Inhibitors of abscisic acid 8′-hydroxylase. Biochemistry 39:13614–13624
Cutler AJ, Squires TM, Loewen MK, Balsevich JJ (1997) Induction of (+)-abscisic acid 8′-hydroxylase by (+)-abscisic acid in cultured maize cells. J Exp Bot 48:1787–1795
Cutler AJ, Krochko JE (1999) Formation and breakdown of ABA. Trend Plant Sci 4:472-478
Desiraju GR, Steiner T (1999) The weak hydrogen bond. Oxford University Press, New York
Durst F, Nelson DR (1995) Diversity and evolution of plant P450 and P450-reductases. Drug Metab Drug Interact 12:189–206
Eisenreich W, Schwarz M, Cartayrade A, Arigoni D, Zenk MH, Bacher A (1998) The deoxyxylulose phosphate pathway of terpenoid biosynthesis in plants and microorganisms. Chem Biol 5:221–233
Fletcher RA, Gilley A, Sankhla N, Davis TD (2001) Triazoles as plant growth regulators and stress protectants. Hortic Rev 24:55–138
Hampson CR, Reaney MJT, Abrams GD, Abrams SR, Gusta LV (1992) Metabolism of (+)-abscisic acid to (+)-7′-hydroxyabscisic acid by bromegrass cell cultures. Phytochemistry 31:2645–2648
Hauser C, Kwiatkowski J, Rademacher W, Grossmann K (1990) Regulation of endogenous abscisic acid levels and transpiration in oilseed rape by plant growth retardants. J plant Physiol 137:201–207
Helliwell CA, Chandler PM, Poole A, Dennis ES, Peacock WJ (2001) The CYP88A cytochrome P450, ent-kaurenoic acid oxidase, catalyzes three steps of the gibberellin biosynthesis pathway. Proc Natl Acad Sci USA 98:2065–2070
Hirai N, Yoshida R, Todoroki Y, Ohigashi H (2000) Biosynthesis of abscisic acid by the non-mevalonate pathway in plants, and by the mevalonate pathway in fungi. Biosci Biotechnol Biochem 64:1448–1458
Hoth S, Morgant M, Sanchez JP, Hanafey MK, Tingey SV, Chua NH (2002) Genome-wide gene expression profiling in Arabidopsis thaliana reveals new targets of abscisic acid and largely impaired gene regulation in the abi1-1 mutant. J Cell Sci 115:4891–4900
Inomata M, Hirai N, Yoshida R, Ohigashi H (2004a) The biosynthetic pathway to abscisic acid via ionylideneethane in the fungus Botrytis cinerea. Phytochemistry 65:2667–78
Inomata M, Hirai N, Yoshida R, Ohigashi H (2004b) Biosynthesis of abscisic acid by the direct pathway via ionylideneethane in a fungus, Cercospora cruenta. Biosci Biotechnol Biochem 68:2571–2580
Iuchi S, Kobayashi M, Taji T, Naramoto M, Seki M, Kato T, Tabata S, Kakubari Y, Yamaguchi-Shinozaki K, Shinozaki K (2001) Regulation of drought tolerance by gene manipulation of 9-cis-epoxycarotenoid dioxygenase, a key enzyme in abscisic acid biosynthesis in Arabidopsis. Plant J 27:325–333
Jennewein S, Rithner CD, Williams RM, Croteau RB (2001) Taxol biosynthesis: taxane 13 alpha-hydroxylase is a cytochrome P450-dependent monooxygenase. Proc Natl Acad Sci USA 98:13595–13600
Jennewein S, Rithner CD, Williams RM, Croteau RB (2003) Taxoid metabolism: Taxoid 14 alpha-hydroxylase is a cytochrome P450-dependent monooxygenase. Arch Biochem Biophys 413:262–270
Kim GT, Tsukaya H, Uchimiya H (1998) The ROTUNDIFOLIA3 gene of Arabidopsis thaliana encodes a new member of the cytochrome P-450 family that is required for the regulated polar elongation of leaf cells. Genes Dev 12:2381–2391
Kitahata N, Saito S, Miyazawa Y, Umezawa T, Shimada Y, Min YK, Mizutani M, Hirai N, Shinozaki K, Yoshida S, Asami T (2005) Chemical regulation of abscisic acid catabolism in plants by cytochrome P450 inhibitors. Bioorg Med Chem 13:4491–4498
Krochko JE, Abrams GD, Loewen MK, Abrams SR, Cutler AJ (1998) (+)-Abscisic acid 8′-hydroxylase is a cytochrome P450 monooxygenase. Plant Physiol 118:849–860
Kushiro T, Okamoto M, Nakabayashi K, Yamagishi K, Kitamura S, Asami T, Hirai N, Koshiba T, Kamiya Y, Nambara E (2004) The Arabidopsis cytochrome P450 CYP707A encodes ABA 8′-hydroxylases: key enzymes in ABA catabolism. EMBO J 23:1647–1656
Lehmann H, Schwenen L (1988) Nigellic acid—an endogenous abscisic acid metabolite from Vicia faba leaves. Phytochemistry 27:677–678
Lim EK, Doucet CJ, Hou B, Jackson R, Abrams SR, Bowles DJ (2005) Resolution of (+)-abscisic acid using an Arabidopsis glycosyltransferase. Tetrahedron: Asymm 16:143–147
Loveys B, Milborrow VB (1991) Hydroxylation of methyl abscisate and the formation of three small alpha-glucosides. Phytochemistry 31:67–72
Milborrow BV (1986) The shapes of abscisic acid and the active site. In: Bopp M (ed) Plant growth substances 1985. Springer-Vertag, Berlin, pp 108–119
Nambara E, Marion-Poll A (2005) Abscisic acid biosynthesis and catabolism. Annu Rev Plant Biol 56:165–185
Oritani T, Kiyota H (2003) Biosynthesis and metabolism of abscisic acid and related compounds. Nat Prod Rep 20:414–425
Priest DM, Ambrose SJ, Vaistij FE., Elias L, Higgins GS, Ross ARS, Abrams SR, Bowles DJ (2006) Use of the glucosyltransferase UGT71B6 to disturb abscisic acid homeostasis in Arabidopsis thaliana. Plant J 46:492–502
Qin X, Zeevaart JAD (2002) Overexpression of a 9-cis-epoxycarotenoid dioxygenase gene in Nicotiana plumbaginifolia increases abscisic acid and phaseic acid levels and enhances drought tolerance. Plant Physiol 128:544–551
Ro DK, Arimura G, Lau SY, Piers E, Bohlmann J (2005) Loblolly pine abietadienol/abietadienal oxidase PtAO (CYP720B1) is a multifunctional, multisubstrate cytochrome P450 monooxygenase. Proc Natl Acad Sci USA 102:8060–8065
Rose PA, Cutler AJ, Irvine NM, Shaw, AC, Squires TM, Loewen MK, Abrams SR (1997) 8′-Acetylene ABA: an irreversible inhibitor of ABA 8′-hydroxylase. Bioorg Med Chem Lett 7:2543–2546
Saito S, Hirai N, Matsumoto C, Ohigashi H, Ohta, D, Sakata K, Mizutani M (2004) Arabidopsis CYP707As encode (+)-Abscisic acid 8′-hydroxylase, a key enzyme in the oxidative catabolism of abscisic acid. Plant Physiol 134:1439–1449
Sawada Y, Aoki M, Noutomi M, Nakaminami K, Mitsuhashi W, Nambara E, Kushiro T, Shinoda S, Kamiya Y, Inoue Y, Toyomasu T (2005) Characterization of genes encoding abscisic acid catabolic enzymes in photoblastic lettuce seeds. Regulation of Plant Growth & Development, vol 40 Supplement 2005. The Japanese Society for Chemical Regulation of Plants, Tokyo
Schmalle VHW, Klaska KH, Jarchow O (1977) Die Kristall- and Molekülstruktur von (R, S)-cis, trans-Abscisinsäure: 5-(1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-2,4-pentadiensaure. Acta Cryst B33:2218–2224
Schoendorf A, Rithner CD, Williams RM, Croteau RB (2001) Molecular cloning of a cytochrome P450 taxane 10 beta-hydroxylase cDNA from Taxus and functional expression in yeast. Proc Natl Acad Sci USA 98:1501–1506
Schuler MA, Werck-Reichhart D (2003) Functional genomics of P450s. Annu Rev Plant Biol 54:629–667
Schwartz SH, Qin X, Zeevaart JA (2003) Elucidation of the indirect pathway of abscisic acid biosynthesis by mutants, genes, and enzymes. Plant Physiol 131:1591–1601
Seo M, Koshiba T (2002) Complex regulation of ABA biosynthesis in plants. Trend Plant Sci 7:41–48
Shimada Y, Fujioka S, Miyauchi N, Kushiro M, Takatsuto S, Nomura T, Yokota T, Kamiya Y, Bishop GJ, Yoshida S (2001) Brassinosteroid-6-oxidases from Arabidopsis and tomato catalyze multiple C-6 oxidations in brassinosteroid biosynthesis. Plant Physiol 26:770–779
Siewers V, Smedsgaard J, Tudzynski P (2004) The P450 monooxygenase BcABA1 is essential for abscisic acid biosynthesis in Botrytis cinerea. Appl Environ Microbiol 70:3868–3876
Szekeres M, Nemeth K, Koncz-Kalman Z, Mathur J, Kauschmann A, Altmann T, Redei GP, Nagy F, Schell J, Koncz C (1996) Brassinosteroids rescue the deficiency of CYP90, a cytochrome P450, controlling cell elongation and de-etiolation in Arabidopsis. Cell 85:171–182
Todoroki Y, Hirai N (2000) Conformational analysis of the cyclohexenone ring in abscisic acid and its analogs with a fused cyclopropyl ring. Tetrahedron 56:8095–8100
Todoroki Y, Hirai H, Ohigashi H (2000) Analysis of isomerization process of 8′-hydroxyabscisic acid and its 3′-fluorinated analog in aqueous solutions. Tetrahedron 56:1649–1653
Todoroki Y, Nakano S, Arai S, Hirai N, Ohigashi H (1997) Synthesis and biological activities of 8′-methylene- and 8′-methylidyneabscisic acids. Biosci Biotechnol Biochem 61:2043-2045
Ueda H, Tanaka J (1977) The crystal and molecular structure of dl-2-cis-4-trans-abscisic acid. Bull Chem Soc Jpn 50:1506–1509
Ueno K, Araki Y, Hirai N, Saito S, Mizutani M, Sakata K, Todoroki Y (2005a) Differences between the structural requirements for ABA 8′-hydroxylase inhibition and for ABA activity. Bioorg Med Chem 13:3359–3370
Ueno K, Saito S, Mizutani M, Sakata K, Hirai N, Todoroki Y (2005b) The functional groups of ABA required for chiral recognition by ABA 8′-hydroxylase. Regulation of Plant Growth & Development, vol 40 Supplement 2005. The Japanese Society for Chemical Regulation of Plants, Tokyo
Ueno K, Yoneyama H, Saito S, Mizutani M, Sakata K, Hirai N, Todoroki Y (2005c) A lead compound for the development of ABA 8′-hydroxylase inhibitors. Bioorg Med Chem Lett 15:5226–5229
Umezawa T, Okamoto M, Kushiro T, Nambara E, Oono Y, Seki M, Kobayashi M, Koshiba T, Kamiya Y, Shinozaki K (2006) CYP707A3, a major ABA 8′-hydroxylase involved in dehydration and rehydration response in Arabidopsis thaliana. Plant J 46:171–182
Wester MR, Yano JK, Schoch GA, Yang C, Griffin KJ, Stout CD, Johnson EF (2004) The structure of human cytochrome P450 2C9 complexed with flurbiprofen at 2.0-Å resolution. J Biol Chem 279:35630–35637
Willows RD, Milborrow BV (1993) Configurations and conformations of abscisic acid. Phytochemistry 34:233–237
Windsor ML, Zeevaart JA (1997) Induction of ABA 8′-hydroxylase by (+)-S-, ( − )-R- and 8′-8′-8′-trifluoro-S-abscisic acid in suspension cultures of potato and Arabidopsis. Phytochemistry 45:931–934
Xiong L, Zhu JK (2003) Regulation of abscisic acid biosynthesis. Plant Physiol 133:29-36
Xu ZJ, Nakajima M, Suzuki Y, Yamaguchi I (2002) Cloning and characterization of the abscisic acid-specific glucosyltransferase gene from adzuki bean seedlings. Plant Physiol 129:1285–1295
Zaharia LI, Gai Y, Nelson KM, Ambrose SJ, Abrams SR (2004) Oxidation of 8′-hydroxy abscisic acid in Black Mexican Sweet maize cell suspension cultures. Phytochemistry 65:3199–3209
Zeevaart JAD, Creelman RA (1988) Metabolism and physiology of abscisic acid. Annu Rev Plant Physiol Plant Mol Biol 39:439–473
Zeevaart JAD, Gage DA, Creelman RA (1990) Recent studies of the metabolism of abscisic acid. In: Pharis RP, Rood SB (eds) Plant growth substances 1988. Springer-Verlag, Berlin, pp 233��240
Zhou R, Cutler AJ, Ambrose SJ, Galka MM, Nelson KM, Squires TM, Loewen MK, Jadhav AS, Ross ARS, Taylor DC, Abrams SR (2004) A new abscisic acid catabolic pathway. Plant Physiol 134:361–369
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Mizutani, M., Todoroki, Y. ABA 8′-hydroxylase and its chemical inhibitors. Phytochem Rev 5, 385–404 (2006). https://doi.org/10.1007/s11101-006-9012-6
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DOI: https://doi.org/10.1007/s11101-006-9012-6